Brönsted acid-mediated intramolecular cyclization of biaryl triazenes for the synthesis of fluorenes and 9,10-dihydro-phenanthrenes

Journal of Organic Chemistry

Volumn 79, Issue 19, 2014, Pages 9206-9221

  Xu, Lijun ^a   Yang, Weijun ^a   Zhang, Lili ^a   Miao, Maozhong ^a   Yang, Zhigen ^a   Xu, Xin ^a   Ren, Hongjun ^a  

^a ZHEJIANG SCI TECH UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENES; INTRAMOLECULAR CYCLIZATIONS; TRIAZENES;

BRONSTED ACID; FLUORENE DERIVATIVE; PHENANTHRENE DERIVATIVE; TRIAZENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 84907802944     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501640d     Document Type: Article

References (59)

1. Watson, M. D.; Fethtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267
2. Chandrasekhar, S. Liq. Cryst. 1993, 14, 3
3. Pérez, D.; Guitián, E. Chem. Soc. Rev. 2004, 33, 274
4. Buess, C. M.; Lawson, D. D. Chem. Rev. 1960, 60, 313
5. Sergeyev, S.; Pisula, W.; Geerts, Y. H. Chem. Soc. Rev. 2007, 36, 1902
6. Freundenmann, R.; Behnisch, B.; Hanack, M. J. Mater. Chem. 2001, 11, 1618
7. Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119
8. van de Craats, A. M.; Stutzmann, N.; Bunk, O.; Nielsen, M. M.; Watson, M.; Müllen, K.; Chanzy, H. D.; Sirringhaus, H.; Friend, R. H. Adv. Mater. 2003, 15, 495
9. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452
10. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718
11. Kaafarani, B. R. Chem. Mater. 2011, 23, 378
12. Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2006, 128, 1434
13. Chernyak, N.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 5636
14. Dai, W.; Petersen, J. L.; Wang, K. K. Org. Lett. 2004, 6, 4355
15. Guo, L.-N.; Duan, X.-H.; Liu, X.-Y.; Hu, J.; Bi, H.-P.; Liang, Y. M. Org. Lett. 2007, 9, 5425
16. Tian, Q.; Larock, R. C. Org. Lett. 2000, 2, 3329
17. Yang, J.-S.; Lee, Y.-R.; Yan, J.-L.; Lu, M.-C. Org. Lett. 2006, 8, 5813
18. Kashulin, I. A.; Nifant'ev, I. E. J. Org. Chem. 2004, 69, 5476
19. Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982
20. Wang, F.; Ueda, W. Chem.-Eur. J. 2009, 15, 742
21. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581
22. Shimizu, M.; Mochida, K.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 9760
23. Hwang, S. J.; Kim, H. J.; Chang, S. Org. Lett. 2009, 11, 4588
24. Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289
25. Liu, T.-P.; Xing, C.-H.; Hu, Q.-S. Angew. Chem., Int. Ed. 2010, 49, 2909
26. Hsiao, C.-C.; Lin, Y.-K.; Liu, C.-J.; Wu, T.-C.; Wu, Y.-T. Adv. Synth. Catal. 2010, 352, 3267
27. Cohen, T.; Lipowitz, J. J. Am. Chem. Soc. 1964, 86, 2515
28. Puskas, I.; Fields, E. K. J. Org. Chem. 1968, 33, 4237
29. Daudpota, A. S.; Heaney, H. Tetrahedron Lett. 1978, 3471
30. Stumpe, R. W. Tetrahedron Lett. 1980, 4891
31. Voica, A.-F.; Mendoza, A.; Gutekunst, W. R.; Fraga, J. O.; Baran, P. S. Nat. Chem. 2012, 4, 629
32. Wang, C.; Chen, H.; Wang, Z.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242
33. Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713
34. Zhou, J.; He, J.; Wang, B.; Yang, W.; Ren, H. J. Am. Chem. Soc. 2011, 133, 6868
35. Zhou, J.; Yang, W.; Wang, B.; Ren, H. Angew. Chem., Int. Ed. 2012, 51, 12293
36. Zhao, G.; Wang, B.; Yang, W.; Ren, H. Eur. J. Org. Chem. 2012, 6236
37. Shang, X.; Xu, L.; Yang, W.; Zhou, J.; Miao, M.; Ren, H. Eur. J. Org. Chem. 2013, 5475
38. Yang, W.; Zhou, J.; Wang, B.; Ren, H. Chem.-Eur. J. 2011, 17, 13665
39. Liu, C.-Y.; Gavryushin, A.; Knochel, P. Chem.-Asian J. 2007, 2, 1020
40. Chen, D.-F.; Han, Z.-Y.; He, Y.-P.; Yu, J.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 12307
41. Pastine, S. J.; McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2005, 127, 12180
42. McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2009, 131, 402
43. Jiao, Z.-W.; Zhang, S.-Y.; He, C.; Tu, Y.-Q.; Wang, S.-H.; Zhang, F.-M.; Zhang, Y.-Q.; Li, H. Angew. Chem., Int. Ed. 2012, 51, 8811
44. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847
45. Mori, K.; Sueoka, S.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 2424
46. Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 6166
47. Fokin, A. A.; Schreiner, P. R. Chem. Rev. 2002, 102, 1551
48. Fokin, A. A.; Schreiner, P. R. Adv. Synth. Catal. 2003, 345, 1035
49. Olah, G. A.; Prakash, G. K. S.; Wade, K.; Molnár, A.; Williams, R. E. Hypercarbon Chemistry, 2 nd ed.; John Wiley & Sons, Inc.: New York, 2011.
50. Fernández, I.; Uggerud, E.; Frenking, G. Chem.-Eur. J. 2007, 13, 8620
51. Yamashita, M.; Yamamoto, Y.; Akiba, K.; Hashizume, D.; Iwasaki, F.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 2005, 127, 4354
52. Siebert, M. R.; Tantillo, D. J. J. Org. Chem. 2006, 71, 645
53. Akiba, K.; Yamashita, M.; Yamamoto, Y.; Nagase, S. J. Am. Chem. Soc. 1999, 121, 10644
54. Perera, S. A.; Bartlett, R. J. J. Am. Chem. Soc. 1996, 118, 7849
55. Campomanes, P.; Suárez, D.; Sordo, T. L. J. Phys. Chem. A 1999, 103, 5996
56. Fornarini, S.; Speranza, M. J. Phys. Chem. 1987, 91, 2154
57. Biermann, U.; Koch, R.; Metzger, J. O. Angew. Chem., Int. Ed. 2006, 45, 3076
58. Anglini, G.; Sparapani, C.; Speranza, M. Tetrahedron. 1984, 40, 4865
59. Colosimo, H.; Speranza, M.; Cacace, F.; Ciranni, G. Tetrahedron 1984, 40, 4873